N-(3H-Thiazol-2-ylidene)nitramine andN-methyl-N-(thiazol-2-yl)nitramine

Abstract

The geometries of the thiazole ring and the nitramino groups in N-(3H-thiazol-2-ylidene)nitramine, C3H3N3O2S, (I), and N-methyl-N-(thiazol-2-yl)nitramine, C4H5N3O2S, (II), are very similar. The nitramine group in (II) is planar and twisted along the C-N bond with respect to the thiazole ring. In both structures, the asymmetric unit includes two practically equal molecules. In (I), the molecules are arranged in layers connected to each other by N-H...N and much weaker C-H...O hydrogen bonds. In the crystal structure of (II), the molecules are arranged in layers bound to each other by both weak C-H...O hydrogen bonds and S...O dipolar interactions.

Crystal structure of S,S′-dimethyl-N-nitroimidodithiocarbonate

“…The similar interaction has previously been observed for 1-nitro-2-methylisourea (II) which is similar in the structure and reactivity in nucleophilic substitution reactions, with the S(1)…O(1) distances being 2.572(7)/2.572(9) Å [7]; and also for other compounds with the >С=NNO 2 nitrimine group directly bonded to the sulfur atom [8,9]. At the same time, compound II had a potentially alternative conformational choice: the orientation of the nitro group to the amino group present in the molecule rather than to the sulfur atom, to form a hydrogen bond between one of the oxygen atoms of the nitro group and the amino group hydrogen.…”

Crystal Structure of S,s'-Dimethyl-N-Nitroimidodithiocarbonate

“…Аналогичное взаимодействие ранее наблюдалось для схожей по строению и реакционной способности в реакциях нуклеофильного замещения 1-нитро-2-метилизотиомочевины (II), расстояние S(1)…O(1) 2,572(7)/2,572(9) Å [ 7 ], а также для других соединений, у которых нитриминная группа >С=NNO 2 непосредственно связана с атомом серы [ 8,9 ]. При этом в соединении II потенциально имелся альтернативный конформационный выбор, ориентация нитрогруппы не на атом серы, а на имеющуюся в молекуле аминогруппу, с образованием водородной связи между одним из атомов кислорода нитрогруппы и водородом аминогруппы.…”